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Check prices for these dates

Next weekend
Apr 24 - Apr 26
In two weeks
May 1 - May 3
In one month
May 15 - May 17
In two months
Jun 12 - Jun 14

Our top choices for Winchester bed & breakfast

Exterior

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (96 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
$309 nightly
The price is $338
May 5 - May 6
Total with taxes and fees
Glen Gordon Manor
Reception

Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (290 reviews)
"Amazing inn, clean, owner is friendly."
United States
Miguel
$138 nightly
The price is $157
Apr 15 - Apr 16
Total with taxes and fees
Loudoun Valley Manor
Front of property

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (677 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
$179 nightly
The price is $198
May 12 - May 13
Total with taxes and fees
Hillbrook Inn
Outdoor dining

The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (67 reviews)
"Quiet setting and friendly owner."
United States
Helen W.
$339 nightly
The price is $386
Apr 15 - Apr 16
Total with taxes and fees
The Van Gogh Room in Villa
Interior

Light Horse Inn: Suite 7

Light Horse Inn: Suite 7
Bolivar
9.2 out of 10, Wonderful, (5 reviews)
"The property was well-kept, and breakfast was delicious with friendly staff and guests."
United States
Rebecca
$195 nightly
The price is $219
Apr 15 - Apr 16
Total with taxes and fees
Light Horse Inn: Suite 7
Front of property

Stone Manor Boutique Inn

Stone Manor Boutique Inn
3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (100 reviews)
"The breakfast was fabulous and the room great "
United States
MICHEL
$230 nightly
The price is $262
Apr 16 - Apr 17
Total with taxes and fees
Stone Manor Boutique Inn
Exterior

Cantuta Inn

Cantuta Inn
3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (76 reviews)
"The hostess and her husband were friendly and made us feel very welcome! Breakfast was scrambled eggs with fruit and was nice."
United States
Ron
$132 nightly
The price is $148
Apr 15 - Apr 16
Total with taxes and fees
Cantuta Inn
Interior

Light Horse Inn: Suite 4

Light Horse Inn: Suite 4
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Very charming and comfortable "
United States
Joseph
$205 nightly
The price is $231
Apr 19 - Apr 20
Total with taxes and fees
Light Horse Inn: Suite 4
Garden

Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (33 reviews)
"Cute place. I enjoyed my room - especially the fireplace and my bed was super comfy. The biergarden was closed so I didn’t get to visit that part of it the property. I had an early flight out of Dulles the next morning so I let her know at check in that I would miss breakfast. Other B&B’s I have stayed at packed me a breakfast to go when I let them know I had to leave early - no such luck here. Which is fine, it’s just a nice touch. So I asked if coffee was possible but nope. A coffee pot in...
United States
Tonya
$296 nightly
The price is $323
Apr 20 - Apr 21
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
Hallway

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (134 reviews)
"Beautiful property and excellent food."
United States
Paula
$268 nightly
The price is $306
May 15 - May 16
Total with taxes and fees
Inn at Evergreen
Porch

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
$359 nightly
The price is $387
Apr 29 - Apr 30
Total with taxes and fees
Gay Street Inn
Outdoor dining

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (37 reviews)
"My husband and I had a memorable stay at Villa Maud over New Year. Maud was a gracious host and we very much enjoyed the comforts of our honeymoon villa. Maud is a talented artist and her impressive work adorns the villa. One of the highlights was meeting Tim the donkey"
United States
jo H.
$423 nightly
The price is $482
Apr 15 - Apr 16
Total with taxes and fees
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Front of property

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (444 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
$156 nightly
The price is $176
Apr 28 - Apr 29
Total with taxes and fees
The Carriage Inn B&B
Interior entrance

The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
$404 nightly
The price is $460
Apr 24 - Apr 25
Total with taxes and fees
The Inn at Grass Roots Hill
Interior

Light Horse Inn: Suite 2

Light Horse Inn: Suite 2
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay. Staff exceptionally friendly"
United States
Michael
$190 nightly
The price is $214
Apr 19 - Apr 20
Total with taxes and fees
Light Horse Inn: Suite 2
Exterior

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."
United States
Daniel F.
$261 nightly
The price is $289
Apr 19 - Apr 20
Total with taxes and fees
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Exterior

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
$13,054 nightly
The price is $15,457
Apr 21 - Apr 22
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Interior

Light Horse Inn: Suite 6

Light Horse Inn: Suite 6
Bolivar
9.8 out of 10, Exceptional, (6 reviews)
"Great spot!"
United States
Theresa
$195 nightly
The price is $219
Apr 16 - Apr 17
Total with taxes and fees
Light Horse Inn: Suite 6
Front of property

Inn of the Shenandoah

Inn of the Shenandoah
4.0 star property
Luray
9.8 out of 10, Exceptional, (40 reviews)
"It was an awesome place to stay!!"
United States
Eileen
$289 nightly
The price is $333
Apr 23 - Apr 24
Total with taxes and fees
Inn of the Shenandoah
Exterior

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (3 reviews)
"My partner and I have both stayed in some pretty high end hotels and we were so impressed!! By far the best VRBO i’ve stayed in-newly renovated and decorated. You don’t want to pass up this hidden gem convenient to everything in Berkeley Springs!"
United States
Deirdre A.
$278 nightly
The price is $309
Apr 16 - Apr 17
Total with taxes and fees
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

10/10 Excellent
"Staff friendly rooms are very clean"
Pamela 1-night trip
Posted 2 hours ago
Sleep Inn & Suites Winchester near University

Find out more about Winchester

Winchester B&B information

Number of reviews
1,345
Accommodation
32 B&B
Lowest Price
$148
Highest Price
$15,457

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $148 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant fall months of September and October. This period attracts travelers looking to experience the stunning autumn foliage and partake in various local events, all while enjoying the comfortable temperatures ranging from the mid-50s to low 70s Fahrenheit. The scenery is particularly enchanting as the leaves change, creating a picturesque backdrop for outdoor activities such as hiking the nearby trails or exploring the charming downtown area.

September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter.
What is the difference between a Winchester Bed & Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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